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Loyola University Chicago

Chemistry: Faculty Publications and Other Works

2007

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Full-Text Articles in Physical Sciences and Mathematics

Isolation Of The Saddle And Crown Conformers Of Cyclotriveratrylene (Ctv) Oxime, Marlon R. Lutz Jr., David C. French, Peter Rehage, Daniel P. Becker Sep 2007

Isolation Of The Saddle And Crown Conformers Of Cyclotriveratrylene (Ctv) Oxime, Marlon R. Lutz Jr., David C. French, Peter Rehage, Daniel P. Becker

Chemistry: Faculty Publications and Other Works

The oxime of cyclotriveratrylene (CTV) has been prepared and the individual crown and saddle conformers were isolated and characterized. The equilibrium constant was measured in CDCl3 and in DMSO-d6 and was shown to favor the crown conformer by an order of magnitude in DMSO-d6, relative to an approximately equal mixture at equilibrium in CDCl3. The time course for interconversion of the saddle to the crown was measured by 1H NMR and the t1/2 of the saddle was determined to be 2.45 h in CDCl3 at 25 °C, and 3.71 h in DMSO-d6.

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2,3,8,12,13-Penta­Meth­Oxy-5h-Dibenzo­[C,N]Acridin-7(6h)-One Toluene Solvate, Marlon R. Lutz Jr, Matthias Zeller, Daniel P. Becker Ph.D. Sep 2007

2,3,8,12,13-Penta­Meth­Oxy-5h-Dibenzo­[C,N]Acridin-7(6h)-One Toluene Solvate, Marlon R. Lutz Jr, Matthias Zeller, Daniel P. Becker Ph.D.

Chemistry: Faculty Publications and Other Works

The title compound, C26H25NO6·C7H8, formed by an unexpected tandem reaction of Beckmann rearrangement, electrophilic aromatic addition and subsequent demethyl­ation, was crystallized as its toluene solvate. The crystal under investigation was found to be nonmerohedrally twinned by a rotation around the reciprocal axis [100]; the twin ratio refined to 0.688 (2):0.312 (2). The mol­ecule exhibits an unusual helical arrangement of three six-membered rings that are all connected at one central C atom. The helix effectively performs one full turn around this atom, and the thread pitch, as defined by the distance of the terminal C atoms of the helix, is 4.98 …

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